JP5242874B2 - Room temperature curable silicone sealant - Google Patents
Room temperature curable silicone sealant Download PDFInfo
- Publication number
- JP5242874B2 JP5242874B2 JP2001553888A JP2001553888A JP5242874B2 JP 5242874 B2 JP5242874 B2 JP 5242874B2 JP 2001553888 A JP2001553888 A JP 2001553888A JP 2001553888 A JP2001553888 A JP 2001553888A JP 5242874 B2 JP5242874 B2 JP 5242874B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- parts
- sealant composition
- silicone sealant
- hydrolyzable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004590 silicone sealant Substances 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 claims description 77
- 229930195733 hydrocarbon Natural products 0.000 claims description 54
- 150000002430 hydrocarbons Chemical class 0.000 claims description 54
- 239000004215 Carbon black (E152) Substances 0.000 claims description 38
- -1 polysiloxane Polymers 0.000 claims description 25
- 229920001296 polysiloxane Polymers 0.000 claims description 24
- 239000012530 fluid Substances 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 21
- 239000000565 sealant Substances 0.000 claims description 20
- 239000012763 reinforcing filler Substances 0.000 claims description 17
- 239000000945 filler Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000002015 acyclic group Chemical group 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 13
- 125000000962 organic group Chemical group 0.000 claims description 12
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 238000013005 condensation curing Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 150000003377 silicon compounds Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- LEEDMQGKBNGPDN-UHFFFAOYSA-N 2-methylnonadecane Chemical compound CCCCCCCCCCCCCCCCCC(C)C LEEDMQGKBNGPDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 claims description 4
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 3
- KXJLGCBCRCSXQF-UHFFFAOYSA-N [diacetyloxy(ethyl)silyl] acetate Chemical compound CC(=O)O[Si](CC)(OC(C)=O)OC(C)=O KXJLGCBCRCSXQF-UHFFFAOYSA-N 0.000 claims description 3
- TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 3
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims description 3
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 3
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 claims description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
- 238000001723 curing Methods 0.000 claims description 2
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 claims description 2
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 claims description 2
- GPTJTTCOVDDHER-UHFFFAOYSA-N cyclononane Chemical compound C1CCCCCCCC1 GPTJTTCOVDDHER-UHFFFAOYSA-N 0.000 claims description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004914 cyclooctane Substances 0.000 claims description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 2
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 claims description 2
- 229940078546 isoeicosane Drugs 0.000 claims description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940094933 n-dodecane Drugs 0.000 claims description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 238000003763 carbonization Methods 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- OPARTXXEFXPWJL-UHFFFAOYSA-N [acetyloxy-bis[(2-methylpropan-2-yl)oxy]silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)(C)C)OC(C)(C)C OPARTXXEFXPWJL-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000007789 sealing Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 1
- JLVYRZKAROXDAS-UHFFFAOYSA-N N-methyl-N-silylacetamide Chemical compound CN([SiH3])C(C)=O JLVYRZKAROXDAS-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- BTHCBXJLLCHNMS-UHFFFAOYSA-N acetyloxysilicon Chemical compound CC(=O)O[Si] BTHCBXJLLCHNMS-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- NCAKWMZPHTZJOT-UHFFFAOYSA-N n-[bis(diethylamino)silyl]-n-ethylethanamine Chemical compound CCN(CC)[SiH](N(CC)CC)N(CC)CC NCAKWMZPHTZJOT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1018—Macromolecular compounds having one or more carbon-to-silicon linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S528/901—Room temperature curable silicon-containing polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
本発明は、一液型室温加硫性シリコーンシーラント、特に流動性と硬化特性とに優れたシーラントに関する。 The present invention relates to a one-pack type room temperature vulcanizable silicone sealant, and particularly to a sealant excellent in fluidity and curing characteristics.
乾燥条件下で保存可能で湿気にさらすと硬化してエラストマーを生成するシリコーン組成物は、建築・建設用途でシーラント及びコーキング材として広く用いられている。こうした組成物は一液型室温加硫性（ＲＴＶ）組成物と呼ばれ、典型的には、湿気硬化性ポリオルガノシロキサンポリマー、充填剤及び縮合硬化触媒を含んでいる。シーラントとして使用する場合、かかる組成物は典型的には防湿チューブに充填され、充填チューブから押出して基材に塗工される。 Silicone compositions that can be stored under dry conditions and cure to form elastomers upon exposure to moisture are widely used as sealants and caulks in building and construction applications. Such compositions are referred to as one-part room temperature vulcanizable (RTV) compositions and typically comprise a moisture curable polyorganosiloxane polymer, a filler and a condensation cure catalyst. When used as a sealant, such compositions are typically filled into moisture-proof tubes and extruded from the filled tubes and applied to a substrate.
シーラント組成物から形成されるエラストマーの性能特性を改良するための方策の一つは、組成物中の充填剤含量を増すことである。しかし、シーラント組成物の充填剤含量を増すと組成物の粘度も上昇し、パッケージから押出すのが困難になる。そこで、当技術分野では、組成物の押出しができるほど十分低い粘度を有する一方で、組成物に添加し得る充填剤量に制限のないシーラント組成物に対するニーズが依然として存在する。 One strategy for improving the performance characteristics of elastomers formed from sealant compositions is to increase the filler content in the composition. However, increasing the filler content of the sealant composition also increases the viscosity of the composition, making it difficult to extrude from the package. Thus, there remains a need in the art for a sealant composition that has a viscosity that is low enough to extrude the composition, while not limiting the amount of filler that can be added to the composition.
本発明は、
（ｉ）加水分解性置換基を有するポリシロキサンポリマーと（ii）２以上の加水分解性置換基を有する多官能性ケイ素化合物との混合物又は反応生成物からなる一液型湿気硬化性ポリシロキサン成分、
充填剤、及び
炭化水素流体１００重量部当り４０重量部を上回る環式パラフィン系炭化水素と６０重量部未満の非環式パラフィン系炭化水素とを含有する炭化水素流体
を含んでなる硬化性シリコーンシーラント組成物に関する。The present invention
A one-component moisture-curable polysiloxane component comprising a mixture or reaction product of (i) a polysiloxane polymer having a hydrolyzable substituent and (ii) a polyfunctional silicon compound having two or more hydrolyzable substituents ,
A curable silicone sealant comprising a filler and a hydrocarbon fluid containing more than 40 parts by weight of a cyclic paraffinic hydrocarbon and less than 60 parts by weight of an acyclic paraffinic hydrocarbon per 100 parts by weight of the hydrocarbon fluid Relates to the composition.
この組成物は容易に押出すごとができ、しかも硬化すると優れた引張特性、伸び及び接着性を示す。 This composition can be easily extruded and, when cured, exhibits excellent tensile properties, elongation and adhesion.
好ましい実施形態では、湿気硬化性シーラントは、シーラント組成物１００重量部当り２０〜９０重量部、さらに好ましくは３０〜７５重量部、さらに一段と好ましくは４０〜６０重量部の湿気硬化性オルガノポリシロキサンポリマー、１〜８０重量部、さらに好ましくは２〜７８重量部、さらに一段と好ましくは３〜６５重量部の充填剤、及び１〜５０重量部、さらに好ましくは１０〜４０重量部、さらに一段と好ましくは１５〜３５重量部の炭化水素流体を含んでなる。 In a preferred embodiment, the moisture curable sealant is 20 to 90 parts by weight, more preferably 30 to 75 parts by weight, even more preferably 40 to 60 parts by weight of moisture curable organopolysiloxane polymer per 100 parts by weight of the sealant composition. 1 to 80 parts by weight, more preferably 2 to 78 parts by weight, even more preferably 3 to 65 parts by weight of filler, and 1 to 50 parts by weight, more preferably 10 to 40 parts by weight, still more preferably 15 -35 parts by weight hydrocarbon fluid.
湿気硬化性ポリシロキサン成分は、（ｉ）加水分解性置換基を有するポリシロキサンポリマーと（ii）２以上の加水分解性置換基を有する多官能性ケイ素化合物との混合物又は反応生成物からなる。 The moisture curable polysiloxane component comprises a mixture or reaction product of (i) a polysiloxane polymer having a hydrolyzable substituent and (ii) a polyfunctional silicon compound having two or more hydrolyzable substituents.
適当な官能性ポリシロキサンは、構造式（Ｉ）の構造単位を有するシリコーンポリマー又はコポリマーを１種以上含む。 Suitable functional polysiloxanes include one or more silicone polymers or copolymers having structural units of structural formula (I).
ＲaＳｉＯ4-a/2 （Ｉ）
式中、Ｒは各々独立にヒドロキシ、加水分解性有機基又は一価炭化水素基であり、０≦ａ≦４であり、１分子当り１以上のＲ基はヒドロキシ基又は加水分解性有機基であり、さらに好ましくはヒドロキシ基である。R a SiO 4-a / 2 (I)
In the formula, each R is independently a hydroxy, a hydrolyzable organic group or a monovalent hydrocarbon group, 0 ≦ a ≦ 4, and one or more R groups per molecule are a hydroxy group or a hydrolyzable organic group. And more preferably a hydroxy group.
適当な加水分解性有機基は、湿気及び縮合硬化触媒の存在下、室温加硫条件下での反応が可能でシーラント組成物を湿気硬化させることのできる有機基であり、例えばアルコキシ、オキシモ、アミノ、アミノキシ又はアシルオキシ基である。 Suitable hydrolyzable organic groups are organic groups that can react under room temperature vulcanization conditions in the presence of moisture and condensation cure catalysts and can cure the sealant composition to moisture, such as alkoxy, oximo, amino An aminoxy or acyloxy group.
適当な一価炭化水素基としては、一価非環式炭化水素基、一価脂環式炭化水素基及び一価芳香族炭化水素基がある。 Suitable monovalent hydrocarbon groups include monovalent acyclic hydrocarbon groups, monovalent alicyclic hydrocarbon groups, and monovalent aromatic hydrocarbon groups.
本明細書中で用いる「一価非環式炭化水素基」という用語は、一価線状又は枝分れ炭化水素基で、好ましくは１基当りの炭素原子数が１〜２０のものを意味するが、これらは飽和基でも不飽和基でもよく、例えば１以上のハロゲン基で適宜置換されていてもよい。適当な一価非環式炭化水素基としては、例えばメチル、エチル、ｓ−ブチル、ｔ−ブチル、オクチル、ドデシル、ステアリル、エイコシルなどのアルキル基、トリフルオロプロピルなどのハロアルキル基、エテニル、プロペニルなどのアルケニル基、及びプロピニル、ブチニルなどのアルキニル基がある。 The term “monovalent acyclic hydrocarbon group” as used herein means a monovalent linear or branched hydrocarbon group, preferably having 1 to 20 carbon atoms per group. However, these may be saturated groups or unsaturated groups, and may be appropriately substituted with, for example, one or more halogen groups. Suitable monovalent acyclic hydrocarbon groups include, for example, alkyl groups such as methyl, ethyl, s-butyl, t-butyl, octyl, dodecyl, stearyl, eicosyl, haloalkyl groups such as trifluoropropyl, ethenyl, propenyl, etc. And alkynyl groups such as propynyl and butynyl.
本明細書中で用いる「脂環式炭化水素基」という用語は、１基当たり１以上の飽和炭化水素環を含む基で、好ましくは環１個当たりの炭素原子数が６〜１０のものを意味するが、１以上の環が１以上のアルキル基（好ましくは１基当たりの炭素原子数が２〜６のもの）で適宜置換されていてもよく、２以上の環を含む場合には縮合環であってもよい。適当な一価脂環式炭化水素基としては、例えばシクロヘキシル及びシクロオクチルがある。 The term “alicyclic hydrocarbon group” as used herein is a group containing one or more saturated hydrocarbon rings per group, preferably those having 6 to 10 carbon atoms per ring. This means that one or more rings may be optionally substituted with one or more alkyl groups (preferably those having 2 to 6 carbon atoms per group), and if two or more rings are included, condensed It may be a ring. Suitable monovalent alicyclic hydrocarbon groups include, for example, cyclohexyl and cyclooctyl.
本明細書中で用いる「単環式芳香族炭化水素基」という用語は、１基当り１つの芳香族環を含む炭化水素基を意味し、芳香族環は１以上のアルキル基（好ましくは１基当たりの炭素原子数が２〜６のもの）で適宜置換されていてもよい。適当な一価芳香族炭化水素基としては、例えばフェニル、トリル、キシリル、２，４，６−トリメチルフェニル及びナフチルがある。 As used herein, the term “monocyclic aromatic hydrocarbon group” means a hydrocarbon group containing one aromatic ring per group, where the aromatic ring is one or more alkyl groups (preferably 1 Optionally having 2 to 6 carbon atoms per group). Suitable monovalent aromatic hydrocarbon groups include, for example, phenyl, tolyl, xylyl, 2,4,6-trimethylphenyl and naphthyl.
好ましい実施形態では、オルガノポリシロキサンポリマーは、構造式（II）の２種以上の線状ポリマー又はコポリマーの混合物を含有する。 In a preferred embodiment, the organopolysiloxane polymer contains a mixture of two or more linear polymers or copolymers of structural formula (II).
式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ9及びＲ10は各々独立に加水分解性有機基又は一価炭化水素基であり、１分子当りＲ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ9及びＲ10の１以上がヒドロキシであるか或いは１分子当りＲ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、Ｒ8、Ｒ9及びＲ10の２以上が加水分解性有機基であり、ｘ及びｙは各々２５℃における粘度が５０００〜５０００００ｃｐのポリマーを与えるように選択された数である。In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently a hydrolyzable organic group or a monovalent hydrocarbon group, One or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 per molecule are hydroxy or R 1 , R 2 , Two or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are hydrolyzable organic groups, and x and y are each a polymer having a viscosity of 5,000 to 500,000 cp at 25 ° C. Is the number chosen to give
好ましい実施形態では、Ｒ1、Ｒ3、Ｒ4、Ｒ5、Ｒ6、Ｒ7、Ｒ8及びＲ9は各々独立にＣ1-8アルキル、フルオロアルキル又はフェニルであり、Ｒ2及びＲ10は各々独立にヒドロキシル、Ｃ1-8アルキル、フルオロアルキル又はフェニルである。In preferred embodiments, R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently C 1-8 alkyl, fluoroalkyl or phenyl, and R 2 and R 10 Each independently is hydroxyl, C 1-8 alkyl, fluoroalkyl or phenyl.
適当な多官能性有機ケイ素化合物は、１分子当り２以上の加水分解性基を有するものである。適当な多官能性有機ケイ素化合物には、シラン類又はシランの部分加水分解生成物があり、例えばビニルトリメトキシシラン、テトラメトキシシラン、メチルトリエトキシシラン、テトラエトキシシラン、メチルトリメトキシシラン、メチルフェニルジエトキシシラン、３，３，３−トリフルオロプロピルトリメトキシシラン、メチル（トリ（メチルエチルケトキシモ）シラン、エチル（トリ（Ｎ，Ｎ−ジエチルアミノ）シラン、メチルトリアセトキシシラン、エチルトリアセトキシシラン、メチルトリ（Ｎ−メチルアセトアミド）シラン、ｎ−プロピルオルトシリケート及びエチルポリシリケート、並びにこれらの化合物の二量体及び三量体が挙げられる。 Suitable polyfunctional organosilicon compounds are those having two or more hydrolyzable groups per molecule. Suitable polyfunctional organosilicon compounds include silanes or silane partial hydrolysis products such as vinyltrimethoxysilane, tetramethoxysilane, methyltriethoxysilane, tetraethoxysilane, methyltrimethoxysilane, methylphenyl. Diethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, methyl (tri (methylethylketoximo) silane, ethyl (tri (N, N-diethylamino) silane, methyltriacetoxysilane, ethyltriacetoxysilane, methyltriacetate (N-methylacetamido) silane, n-propylorthosilicate and ethylpolysilicate, and dimers and trimers of these compounds.
好ましい実施形態では、多官能性有機ケイ素化合物は構造式（III）を有する。 In a preferred embodiment, the polyfunctional organosilicon compound has the structural formula (III).
Ｒ11 4Ｓｉ （III）
式中、Ｒ11は、１以上のＲ11基がＨ、アルコキシ又はアルケニルで２以上のＲ11基が加水分解性基であることを条件として、各々独立に加水分解性基又は一価炭化水素基である。R 11 4 Si (III)
Wherein R 11 is independently a hydrolyzable group or monovalent hydrocarbon, provided that one or more R 11 groups are H, alkoxy or alkenyl and two or more R 11 groups are hydrolyzable groups. It is a group.
好ましい実施形態では、Ｒ11置換基の３以上は各々、アルコキシ、オキシモ、アミノ、アミノキシ又はアシルオキシ、さらに好ましくはアルコキシ又はアシルオキシ、さらに一段と好ましくはＣ1-8アルコキシ又はＣ1-8アシルオキシであり、残りのＲ11置換基がある場合はＣ1-8アルキル、Ｃ2-8アルケニル、アリール又はフルオロアルキルである。好ましい多官能性有機ケイ素化合物としては、例えばビニルトリメトキシシラン、テトラメトキシシラン、メチルトリエトキシシラン、メチルトリアセトキシシラン、エチルトリアセトキシシラン、テトラエトキシシラン、メチルトリメトキシシラン、ジ−ｔ−ブトキシジアセトキシシラン又はこれらの混合物が挙げられる。In a preferred embodiment, three or more of the R 11 substituents are each alkoxy, oximo, amino, aminoxy or acyloxy, more preferably alkoxy or acyloxy, even more preferably C 1-8 alkoxy or C 1-8 acyloxy, If there are remaining R 11 substituents, it is C 1-8 alkyl, C 2-8 alkenyl, aryl or fluoroalkyl. Preferred polyfunctional organosilicon compounds include, for example, vinyltrimethoxysilane, tetramethoxysilane, methyltriethoxysilane, methyltriacetoxysilane, ethyltriacetoxysilane, tetraethoxysilane, methyltrimethoxysilane, di-t-butoxydi. Acetoxysilane or a mixture thereof may be mentioned.
各ケイ素含有成分の相対量は当業者が容易に決定できる。一般に、湿気硬化性オルガノポリシロキサンポリマーは、１００重量部のオルガノポリシロキサンポリマーと、約０．１〜１５重量部、さらに好ましくは約１．０〜１０重量部、最も好ましくは約２〜７重量部の多官能性有機ケイ素化合物との反応で製造される。 The relative amount of each silicon-containing component can be readily determined by one skilled in the art. In general, the moisture curable organopolysiloxane polymer is 100 parts by weight organopolysiloxane polymer and about 0.1 to 15 parts by weight, more preferably about 1.0 to 10 parts by weight, most preferably about 2 to 7 parts by weight. Produced by reaction with some polyfunctional organosilicon compounds.
少なくとも若干の湿気硬化性オルガノポリシロキサンポリマーは、本発明の組成物の配合時に、オルガノポリシロキサンポリマーと多官能性有機ケイ素化合物とのその場での縮合反応によって形成されると考えられる。 It is believed that at least some moisture curable organopolysiloxane polymer is formed by an in situ condensation reaction between the organopolysiloxane polymer and the polyfunctional organosilicon compound upon formulation of the composition of the present invention.
本発明の組成物は、任意成分として縮合硬化触媒をさらに含んでいてもよい。適当な縮合硬化触媒には、湿気の存在下、架橋性オルガノポリシロキサンポリマーの室温架橋を触媒するものがあり、例えばジブチルスズジラウレート、ジブチルスズジアセテート、スズ２−エチルヘキサノエートなどのジアルキルスズカルボキシレート、テトラブチルスズチタネート、テトラ−ｎ−プロピルチタネートなどのアルキルチタネート及びオルガノシロキシチタン化合物が挙げられる。その他各種の縮合触媒が当技術分野で公知である。 The composition of the present invention may further contain a condensation curing catalyst as an optional component. Suitable condensation cure catalysts include those that catalyze the room temperature crosslinking of crosslinkable organopolysiloxane polymers in the presence of moisture, such as dialkyltin carboxylates such as dibutyltin dilaurate, dibutyltin diacetate, tin 2-ethylhexanoate. , Alkyl titanates such as tetrabutyltin titanate and tetra-n-propyl titanate, and organosiloxytitanium compounds. Various other condensation catalysts are known in the art.
多官能性有機ケイ素化合物がアシルオキシ置換基を含む場合、組成物は、組成物１００重量部当り０〜１重量部、さらに好ましくは０．０１〜０．５重量部のジアルキルスズカルボキシレート縮合硬化触媒を含む。 When the polyfunctional organosilicon compound contains an acyloxy substituent, the composition is 0 to 1 part by weight, more preferably 0.01 to 0.5 part by weight dialkyl tin carboxylate condensation cure catalyst per 100 parts by weight of the composition. including.
多官能性有機ケイ素化合物がアシルオキシ基以外の加水分解性有機基を含む場合、組成物は、組成物１００重量部当り０．０１〜１０重量部、さらに好ましくは０．１〜７重量部、さらに一段と好ましくは１〜５重量部のアルキルチタネート又はオルガノシロキシチタン化合物の縮合硬化触媒を含む。 When the polyfunctional organosilicon compound contains a hydrolyzable organic group other than an acyloxy group, the composition is 0.01 to 10 parts by weight, more preferably 0.1 to 7 parts by weight per 100 parts by weight of the composition, More preferably 1 to 5 parts by weight of an alkyl titanate or organosiloxy titanium compound condensation cure catalyst.
多官能性有機ケイ素化合物がアシルオキシ基以外の加水分解性有機基を含む場合、組成物は、組成物１００重量部当り０．０１〜５重量部、好ましくは０．０５〜２重量部、さらに好ましくは０．１〜０．３重量部のジアルキルスズカルボキシレート縮合硬化触媒を含む。 When the polyfunctional organosilicon compound contains a hydrolyzable organic group other than an acyloxy group, the composition is 0.01 to 5 parts by weight, preferably 0.05 to 2 parts by weight, more preferably 100 parts by weight of the composition Contains 0.1 to 0.3 parts by weight of a dialkyltin carboxylate condensation cure catalyst.
炭化水素流体は通例１分子当りの炭素原子数が５〜２４の環式炭化水素を１種以上含み、任意には１分子当りの炭素原子数が５〜２４の非環式パラフィン系炭化水素を１種以上含有する。好ましい実施形態では、炭化水素流体の環式炭化水素及び非環式炭化水素は各々１分子当りの炭素原子数が８〜２０、さらに好ましくは１０〜１５である。適当な環式パラフィン系炭化水素としては、例えばシクロヘキサン、シクロオクタン、シクロノナン、シクロデカン及びシクロドデカンがある。適当な非環式パラフィン系炭化水素としては、例えばｎ−ヘプタン、ｎ−ヘキサン、ｎ−オクタン、イソオクタン、ｎ−ノナン、ｎ−デカン、ｎ−ウンデカン、ｎ−ドデカン、イソドデカン、ｎ−ヘプタデカン、ｎ−オクタデカン、ｎ−エイコサン、イソエイコサンがある。好ましい実施形態では、炭化水素流体は芳香族炭化水素含量約０．５重量％未満である。 The hydrocarbon fluid typically contains one or more cyclic hydrocarbons having 5 to 24 carbon atoms per molecule, and optionally an acyclic paraffinic hydrocarbon having 5 to 24 carbon atoms per molecule. Contains one or more. In a preferred embodiment, the cyclic and non-cyclic hydrocarbons of the hydrocarbon fluid each have 8 to 20 carbon atoms per molecule, more preferably 10 to 15 carbon atoms. Suitable cyclic paraffinic hydrocarbons include, for example, cyclohexane, cyclooctane, cyclononane, cyclodecane and cyclododecane. Suitable acyclic paraffinic hydrocarbons include, for example, n-heptane, n-hexane, n-octane, isooctane, n-nonane, n-decane, n-undecane, n-dodecane, isododecane, n-heptadecane, n -Octadecane, n-eicosane, isoeicosane. In a preferred embodiment, the hydrocarbon fluid has an aromatic hydrocarbon content of less than about 0.5% by weight.
好ましい実施形態では、炭化水素流体は、炭化水素流体１００重量部当り約４２〜１００重量部、さらに好ましくは約４５〜７５重量部、さらに一段と好ましくは約５０〜７０重量部、特に好ましくは約５５〜６５重量部の環式パラフィン系炭化水素と、０〜５８重量部、さらに好ましくは約２５〜５５重量部、さらに一段と好ましくは約３０〜５０重量部、特に好ましくは約３０〜４５重量部の非環式（すなわち線状又は枝分れ）パラフィン系炭化水素を含む。好ましい実施形態では、炭化水素流体はノルマル（すなわち線状）パラフィン系炭化水素の含量が１５重量部未満、さらに好ましくは１０重量部未満である。 In a preferred embodiment, the hydrocarbon fluid is about 42-100 parts by weight per 100 parts by weight hydrocarbon fluid, more preferably about 45-75 parts by weight, even more preferably about 50-70 parts by weight, particularly preferably about 55 parts by weight. ~ 65 parts by weight of a cyclic paraffinic hydrocarbon and 0 to 58 parts by weight, more preferably about 25 to 55 parts by weight, still more preferably about 30 to 50 parts by weight, particularly preferably about 30 to 45 parts by weight. Includes acyclic (ie, linear or branched) paraffinic hydrocarbons. In a preferred embodiment, the hydrocarbon fluid has a normal (ie, linear) paraffinic hydrocarbon content of less than 15 parts by weight, more preferably less than 10 parts by weight.
充填剤成分は概して補強充填剤、半補強充填剤、非補強充填剤又はこれらの混合物である。好ましくは、充填剤は補強型であり、例えばヒュームドシリカ、疎水化ヒュームドシリカ、カーボンブラック、二酸化チタン、酸化第二鉄、酸化アルミニウムその他の金属酸化物である。これらの充填剤は、多くの供給元から市販されている。ヒュームドシリカが好ましい。硬化性シリコーンシーラント組成物は、シーラント組成物１００重量部当り１〜２０重量部、さらに好ましくは５〜１５重量部の補強充填剤を含有し得る。 The filler component is generally a reinforcing filler, a semi-reinforcing filler, a non-reinforcing filler or a mixture thereof. Preferably, the filler is reinforced, such as fumed silica, hydrophobized fumed silica, carbon black, titanium dioxide, ferric oxide, aluminum oxide or other metal oxide. These fillers are commercially available from a number of suppliers. Fumed silica is preferred. The curable silicone sealant composition may contain 1 to 20 parts by weight, more preferably 5 to 15 parts by weight of reinforcing filler per 100 parts by weight of the sealant composition.
硬化性シーラント組成物に使用する充填剤は、適宜半補強充填剤又は非補強充填剤をさらに含んでいてもよい。適当な半補強充填剤又は非補強充填剤としては、例えば石英、沈降シリカ、疎水化沈降シリカ及び炭酸カルシウムがあり、これらは多くの供給元から市販されている。好ましい実施形態では、半補強充填剤又は非補強充填剤は炭酸カルシウムである。半補強充填剤又は非補強充填剤を含有する場合、シリコーンシーラント組成物は、シーラント組成物１００重量部当り０〜７０重量部、さらに好ましくは３０〜６０重量部、さらに一段と好ましくは４０〜６０重量部の半補強充填剤、非補強充填剤又はこれらの混合物を含有する。 The filler used in the curable sealant composition may further include a semi-reinforcing filler or a non-reinforcing filler as appropriate. Suitable semi-reinforcing fillers or non-reinforcing fillers include, for example, quartz, precipitated silica, hydrophobized precipitated silica and calcium carbonate, which are commercially available from a number of suppliers. In a preferred embodiment, the semi-reinforcing filler or non-reinforcing filler is calcium carbonate. When containing a semi-reinforcing filler or non-reinforcing filler, the silicone sealant composition is 0 to 70 parts by weight, more preferably 30 to 60 parts by weight, even more preferably 40 to 60 parts by weight per 100 parts by weight of the sealant composition. Part semi-reinforcing fillers, non-reinforcing fillers or mixtures thereof.
硬化性シリコーンシーラント組成物は、任意成分として、その他の公知成分、例えば染料、顔料、酸化防止剤、ＵＶ安定剤、接着増強剤、ステアリン酸アルミニウムなどの熱安定剤、殺生剤、非シリコーン系ポリマー、及びポリエチレングリコールやポリプロピレングリコールなどのチキソトロープ剤を含んでいてもよい。 The curable silicone sealant composition may optionally include other known components such as dyes, pigments, antioxidants, UV stabilizers, adhesion enhancers, heat stabilizers such as aluminum stearate, biocides, and non-silicone polymers. , And thixotropic agents such as polyethylene glycol and polypropylene glycol.
硬化性シーラント組成物は組成物の各種成分を一緒に混合することで製造される。混合は回分法でも連続法でも実施でき、成分の混合にはプラネタリーミキサーなど適当な混合装置を使用すればよい。好ましい実施形態では、組成物は、押出機、好ましくは二軸押出機で組成物を連続的に配合することにより製造される。 The curable sealant composition is produced by mixing together the various components of the composition. Mixing can be carried out by a batch method or a continuous method, and an appropriate mixing apparatus such as a planetary mixer may be used for mixing the components. In a preferred embodiment, the composition is made by continuously blending the composition in an extruder, preferably a twin screw extruder.
使用に当たり、組成物を例えば押出して周囲湿気にさらして硬化させる。好ましくは、組成物は使用時まで防湿性パッケージ中に保持する。好ましい実施形態では、本発明の組成物は第２基材が第１基材から離間して隙間をなしている第１基材と第２基材との間の隙間を封止するのに使用され、組成物を隙間を埋めるのに有効な量塗工し、組成物をその場で硬化させて基材間にエラストマーシールを形成する。 In use, the composition is, for example, extruded and cured by exposure to ambient moisture. Preferably, the composition is kept in a moisture-proof package until use. In a preferred embodiment, the composition of the present invention is used to seal a gap between a first substrate and a second substrate where the second substrate is spaced apart from the first substrate. The composition is coated in an effective amount to fill the gaps and the composition is cured in situ to form an elastomeric seal between the substrates.
本発明のさらに他の実施形態は、第１基材と、第１基材から離間した第２基材と、請求項１のシリコーンシーラント組成物の硬化物とを含んでなるアセンブリに関する。 Yet another embodiment of the present invention relates to an assembly comprising a first substrate, a second substrate spaced from the first substrate, and a cured product of the silicone sealant composition of claim 1.
以下の非限定的な実施例で本発明をさらに例示する。 The invention is further illustrated in the following non-limiting examples.
本実施例のシーラント組成物はアセトキシシーラントであって、ヒドロキシ末端ポリジメチルシロキサンポリマー６７．２重量％、炭化水素流体２０重量％、未処理ヒュームドシリカ９重量％、触媒溶液３．５重量％及び他の添加剤０．３重量％からなる。触媒溶液はアセトキシ官能性シラン架橋剤及び縮合硬化触媒を含んでいた。炭化水素流体（Ｃｏｎｏｓｏｌ（商標）Ｃ−２００炭化水素流体）の公称組成は、環式パラフィン系炭化水素約６０重量％、ｎ−パラフィン系炭化水素５〜６重量％及び残部のイソパラフィン系炭化水素からなり、芳香族炭化水素含量は約０．５重量％未満であった。シーラント組成物を７５℃、相対湿度５０％で７日間硬化した後、物性について試験した。使用したＡＳＴＭ試験及び試験結果を下表に示す。 The sealant composition of this example is an acetoxy sealant, comprising 67.2 wt% hydroxy-terminated polydimethylsiloxane polymer, 20 wt% hydrocarbon fluid, 9 wt% untreated fumed silica, 3.5 wt% catalyst solution and It consists of 0.3% by weight of other additives. The catalyst solution contained an acetoxy functional silane crosslinker and a condensation cure catalyst. The nominal composition of the hydrocarbon fluid (Conosol ™ C-200 hydrocarbon fluid) is from about 60% by weight of cyclic paraffinic hydrocarbon, 5-6% by weight of n-paraffinic hydrocarbon and the balance isoparaffinic hydrocarbon. The aromatic hydrocarbon content was less than about 0.5% by weight. The sealant composition was cured for 7 days at 75 ° C. and 50% relative humidity and then tested for physical properties. The ASTM test and test results used are shown in the table below.
上記のデータから分かるように、上記硬化性組成物は優れた物性を有する。 As can be seen from the above data, the curable composition has excellent physical properties.
好ましい実施形態を示し説明したが、本発明の要旨から逸脱することなく、種々の変更及び代替が可能である。したがって、本発明の説明は例示のためのものであって、限定のためのものではない。 While the preferred embodiment has been shown and described, various modifications and alternatives can be made without departing from the spirit of the invention. Accordingly, the description of the present invention is intended to be illustrative and not limiting.
Claims (17)
（ｉ）加水分解性置換基を有するポリシロキサンポリマーと（ｉｉ）２以上の加水分解性置換基を有する多官能性ケイ素化合物との混合物又は反応生成物からなる一液型湿気硬化性ポリシロキサン成分、
充填剤、
縮合硬化触媒、及び
炭化水素流体１００重量部当り４５〜７５重量部の環式パラフィン系炭化水素と２５〜５５重量部の非環式パラフィン系炭化水素とを含有し、芳香族炭化水素の含量が０．５重量％未満であり、芳香族炭化水素以外は環式パラフィン系炭化水素と非環式パラフィン系炭化水素のみからなり、ノルマルパラフィン系炭化水素の含量が炭化水素流体１００重量部当り１５重量部未満である炭化水素流体を含んでなる硬化性シリコーンシーラント組成物。
One-component moisture-curable polysiloxane component comprising a mixture or reaction product of (i) a polysiloxane polymer having a hydrolyzable substituent and (ii) a polyfunctional silicon compound having two or more hydrolyzable substituents ,
filler,
Condensation curing catalyst and 45 to 75 parts by weight of cyclic paraffinic hydrocarbon and 25 to 55 parts by weight of acyclic paraffinic hydrocarbon per 100 parts by weight of hydrocarbon fluid, the content of aromatic hydrocarbons It is less than 0.5% by weight and consists of only cyclic paraffinic hydrocarbons and acyclic paraffinic hydrocarbons other than aromatic hydrocarbons, and the content of normal paraffinic hydrocarbons is 15 weights per 100 parts by weight of hydrocarbon fluid. A curable silicone sealant composition comprising less than part hydrocarbon fluid.
2. The composition of claim 1 comprising 20 to 90 parts by weight moisture curable organopolysiloxane polymer, 1 to 80 parts by weight filler and 1 to 50 parts by weight hydrocarbon fluid per 100 parts by weight of the sealant composition. Curable silicone sealant composition.
The moisture curable polysiloxane component comprises a mixture or reaction product of (i) a polysiloxane polymer having a hydrolyzable substituent and (ii) a polyfunctional silicon compound having two or more hydrolyzable substituents. The curable silicone sealant composition according to claim 1.
ＲａＳｉＯ４−ａ／２ （Ｉ）
式中、Ｒは各々独立にヒドロキシ、加水分解性有機基又は一価炭化水素基であり、０≦ａ≦４であり、１分子当り１以上のＲ基はヒドロキシ又は加水分解性有機基である。
The curable silicone sealant composition of claim 3, wherein the functional polysiloxane comprises one or more silicone polymers or copolymers having structural units of the following structural formula (I):
R a SiO 4-a / 2 (I)
In the formula, each R is independently a hydroxy, hydrolyzable organic group or monovalent hydrocarbon group, 0 ≦ a ≦ 4, and one or more R groups per molecule are hydroxy or hydrolyzable organic groups. .
【化１】
式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｒ８、Ｒ９及びＲ１０は各々独立に加水分解性有機基又は一価炭化水素基であり、１分子当りＲ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｒ８、Ｒ９及びＲ１０の１以上がヒドロキシであるか或いは１分子当りＲ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｒ８、Ｒ９及びＲ１０の２以上が加水分解性有機基であり、ｘ及びｙは各々２５℃における粘度が５０００〜５０００００ｃｐのポリマーを与えるように選択された数である。
The curable silicone sealant composition of claim 4, wherein the organopolysiloxane polymer comprises a mixture of two or more linear polymers or copolymers of structural formula (II).
[Chemical 1]
In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently a hydrolyzable organic group or a monovalent hydrocarbon group, One or more of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 per molecule are hydroxy or R 1 , R 2 , Two or more of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are hydrolyzable organic groups, and x and y are each a polymer having a viscosity of 5000 to 500,000 cp at 25 ° C. Is the number chosen to give
The curable silicone sealant composition according to claim 3, wherein the polyfunctional organosilicon compound has two or more hydrolyzable groups per molecule.
Ｒ１１ ４Ｓｉ （ＩＩＩ）
式中、Ｒ１１は、１以上のＲ１１基がＨ、アルコキシ又はアルケニルで２以上のＲ１１基が加水分解性基であることを条件として、各々独立に加水分解性基又は一価炭化水素基である。
The curable silicone sealant composition of claim 6, wherein the polyfunctional organosilicon compound has the structural formula (III).
R 11 4 Si (III)
Wherein R 11 is independently a hydrolyzable group or monovalent hydrocarbon, provided that one or more R 11 groups are H, alkoxy or alkenyl and two or more R 11 groups are hydrolyzable groups. It is a group.
The curable silicone sealant composition of claim 7, wherein the three or more R 11 substituents are each alkoxy, oximo, amino, aminoxy, or acyloxy.
3. The three or more R 11 substituents are C 1-8 alkoxy or C 1-8 acyloxy, and the remaining R 11 substituents are C 1-8 alkyl, C 2-8 alkenyl, aryl or fluoroalkyl. 8. The curable silicone sealant composition according to 7.
The polyfunctional organosilicon compound is vinyltrimethoxysilane, tetramethoxysilane, methyltriethoxysilane, methyltriacetoxysilane, ethyltriacetoxysilane, tetraethoxysilane, methyltrimethoxysilane, di-t-butoxydiacetoxysilane or The curable silicone sealant composition according to claim 7, which is a mixture thereof.
The hydrocarbon fluid contains one or more cyclic paraffinic hydrocarbons having 5 to 24 carbon atoms per molecule, and acyclic paraffinic hydrocarbons having 5 to 24 carbon atoms per molecule. The curable silicone sealant composition according to claim 1, comprising one or more.
The cyclic paraffinic hydrocarbon is cyclohexane, cyclooctane, cyclononane, cyclodecane or cyclododecane, and the acyclic paraffinic hydrocarbon is n-heptane, n-hexane, n-octane, isooctane, n-nonane, n The curable silicone sealant composition of claim 11, which is -decane, n-undecane, n-dodecane, isododecane, n-heptadecane, n-octadecane, n-eicosane or isoeicosane.
The curable silicone sealant composition of claim 1, wherein the filler is a reinforcing filler and is present in an amount of 1 to 20 parts by weight per 100 parts by weight of the total sealant composition.
The curable silicone sealant composition of claim 13 further comprising a semi-reinforcing filler or a non-reinforcing filler.
（ｉ）加水分解性置換基を有するポリシロキサンポリマーと（ｉｉ）２以上の加水分解性置換基を有する多官能性ケイ素化合物との混合物又は反応生成物からなる一液型湿気硬化性ポリシロキサン成分と、
充填剤と、
縮合硬化触媒と、
炭化水素流体１００重量部当り４５〜７５重量部の環式パラフィン系炭化水素と２５〜５５重量部の非環式パラフィン系炭化水素とを含有し、芳香族炭化水素の含量が０．５重量％未満であり、芳香族炭化水素以外は環式パラフィン系炭化水素と非環式パラフィン系炭化水素のみからなり、ノルマルパラフィン系炭化水素の含量が炭化水素流体１００重量部当り１５重量部未満である炭化水素流体とを混合する工程を含んでなる方法。
A method for producing a one-component room temperature curable sealant composition comprising:
One-component moisture-curable polysiloxane component comprising a mixture or reaction product of (i) a polysiloxane polymer having a hydrolyzable substituent and (ii) a polyfunctional silicon compound having two or more hydrolyzable substituents When,
A filler,
A condensation curing catalyst;
Contains the acyclic paraffinic hydrocarbons, cyclic paraffinic hydrocarbons and 25 to 55 parts by weight of the hydrocarbon fluid 100 parts by weight per 45 to 75 parts by weight, the content of aromatic hydrocarbons of 0.5 wt% The carbonization consists of cyclic paraffinic hydrocarbons and non-cyclic paraffinic hydrocarbons other than aromatic hydrocarbons, and the content of normal paraffinic hydrocarbons is less than 15 parts by weight per 100 parts by weight of hydrocarbon fluid. A method comprising the step of mixing with a hydrogen fluid.
（ｉ）加水分解性置換基を有するポリシロキサンポリマーと（ｉｉ）２以上の加水分解性置換基を有する多官能性ケイ素化合物との混合物又は反応生成物からなる一液型湿気硬化性ポリシロキサン成分、充填剤、縮合硬化触媒、及び炭化水素流体１００重量部当り４５〜７５重量部の環式パラフィン系炭化水素と２５〜５５重量部の非環式パラフィン系炭化水素とを含有し、芳香族炭化水素の含量が０．５重量％未満であり、芳香族炭化水素以外は環式パラフィン系炭化水素と非環式パラフィン系炭化水素のみからなり、ノルマルパラフィン系炭化水素の含量が炭化水素流体１００重量部当り１５重量部未満である炭化水素流体を含んでなる室温硬化性シーラント組成物を上記隙間を埋めるのに有効な量塗工し、次いで
上記組成物をその場で硬化させて基材間にエラストマーシールを形成する工程を含んでなる方法。
A method of sealing a gap between a first base material and a second base material in which the second base material is spaced apart from the first base material,
One-component moisture-curable polysiloxane component comprising a mixture or reaction product of (i) a polysiloxane polymer having a hydrolyzable substituent and (ii) a polyfunctional silicon compound having two or more hydrolyzable substituents Containing 45 to 75 parts by weight of cyclic paraffinic hydrocarbon and 25 to 55 parts by weight of acyclic paraffinic hydrocarbon per 100 parts by weight of hydrocarbon fluid, filler, condensation curing catalyst, and aromatic carbonization The hydrogen content is less than 0.5% by weight, and other than aromatic hydrocarbons are composed of only cyclic paraffinic hydrocarbons and acyclic paraffinic hydrocarbons, and the content of normal paraffinic hydrocarbons is 100 wt. A room temperature curable sealant composition comprising less than 15 parts by weight hydrocarbon fluid is applied in an amount effective to fill the gap, and then the composition is applied in situ. A method comprising the step of curing to form an elastomeric seal between substrates.
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| MXPA02011492A (en) * | 2001-12-03 | 2003-06-30 | Rohm & Haas | Moisture-curing adhesives. |
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-
2001
- 2001-01-19 WO PCT/US2001/001841 patent/WO2001053425A2/en active Application Filing
- 2001-01-19 CA CA2396485A patent/CA2396485C/en not_active Expired - Lifetime
- 2001-01-19 EP EP01942656A patent/EP1252252B1/en not_active Revoked
- 2001-01-19 AU AU2001229648A patent/AU2001229648A1/en not_active Abandoned
- 2001-01-19 EP EP10011312.5A patent/EP2292714B1/en not_active Expired - Lifetime
- 2001-01-19 JP JP2001553888A patent/JP5242874B2/en not_active Expired - Lifetime
- 2001-01-19 US US09/766,507 patent/US6451440B2/en not_active Expired - Lifetime
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| EP1252252A2 (en) | 2002-10-30 |
| US20010049427A1 (en) | 2001-12-06 |
| JP2003520886A (en) | 2003-07-08 |
| EP2292714A1 (en) | 2011-03-09 |
| CA2396485C (en) | 2010-12-07 |
| CA2396485A1 (en) | 2001-07-26 |
| EP1252252B1 (en) | 2012-09-19 |
| WO2001053425A2 (en) | 2001-07-26 |
| US6451440B2 (en) | 2002-09-17 |
| AU2001229648A1 (en) | 2001-07-31 |
| JP2013100519A (en) | 2013-05-23 |
| EP2292714B1 (en) | 2016-03-30 |
| WO2001053425A3 (en) | 2002-02-14 |
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